Iron-catalyzed oxidative C-C(vinyl) σ-bond cleavage of allylarenes to aryl aldehydes at room temperature with ambient air.
CHEMICAL COMMUNICATIONS(2019)
Abstract
A general and selective iron-catalyzed allylic C-C(vinyl) sigma-bond cleavage of allylarenes without the assistance of heteroatoms to give aryl aldehydes is reported. The unstrained carbon-carbon single bond cleavage reaction uses ambient air as the sole oxidant, proceeds efficiently at room temperature, and allows for exceptional functional-group tolerance, which addresses the long-standing challenges of current C-C bond cleavage/functionalization. Notably, the method enables rapid late-stage oxidation of complex bioactive molecules and can be used to expedite syntheses of natural products (vanillin and glucovanillin) from readily available chemical feedstocks.
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Key words
allylarenes,aryl aldehydes,iron-catalyzed
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